HCID 86590695, compound → HCID 69053107, compound

HRID 1866168Notes

Reaction equation

HRID 1866168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([OH:21])[CH2:10][NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH:5]=[N:6][C:7]=1Cl>C(O)(=O)C.O.[Br-].C[N+](C)(C)C.C(OCC)(=O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([OH:21])[CH2:10][NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 1

HCID 86590695HCID 86590695, compound

Product 1

HCID 69053107HCID 69053107, compoundYield 65.7%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 66137Tetramethylammonium bromideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-[2-[[(2R)-2-(5,6-dichloro-3-pyridyl)-2-hydroxyethyl)amino]ethyl]phenol (850 mg) in acetic acid (15 ml) and water (1.0 ml) were added tetramethylammonium bromide (5.2 mg) and zinc dust (509 mg), and the mixture was stirred at 50° C. for 10 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 4-[2-[[(2R)-2-(5-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]phenol (500 mg) as a colorless oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-a827dc6c2241468f8e44b6e61fe54f99
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

Loading…